Process for xylene production with energy optimization

ABSTRACT

A method for producing xylenes from a heavy reformate feed includes the steps of introducing the heavy reformate feed and a hydrogen feed to a dealkylation reactor, reacting the heavy reformate feed with the hydrogen gas in the presence of the dealkylation catalyst in the dealkylation reactor to produce a dealkylation effluent, introducing the dealkylation effluent to a splitter unit, separating the dealkylation effluent into a light gas stream, a toluene stream, a benzene stream, a C9 aromatics stream, a C10+ aromatics stream, and a mixed xylene stream in the splitter unit, introducing the toluene stream, the C9 aromatics stream, and a hydrogen stream into a transalkylation reactor, reacting the toluene stream and the C9 aromatics stream in the presence of the transalkylation catalyst to produce a transalkylation effluent, introducing the transalkylation effluent to the splitter unit, and separating the transalkylation effluent in the splitter unit.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a continuation application of U.S. patentapplication Ser. No. 16/173,412 filed on Oct. 29, 2018, which claimspriority from U.S. patent application Ser. No. 16/018,394 filed on Jun.26, 2018, which claims priority from U.S. patent application Ser. No.15/606,600 filed on May 26, 2017, issued on Jul. 31, 2018 as U.S. Pat.No. 10,035,742. For purposes of United States patent practice, thisapplication incorporates the contents of both Non-ProvisionalApplications by reference in their entirety.

TECHNICAL FIELD

Disclosed are methods and systems for production of xylenes.Specifically, disclosed are methods and systems for production ofxylenes from heavy aromatics.

BACKGROUND

Heavy reformate can include greater than 90 percent by weight (wt %)aromatics with eight or more carbon atoms in the aromatic compound. Ofthe aromatics, less than or equal to 10 wt % can be xylenes. In pastpractice, the heavy reformate was blended into the gasoline stream.However, blending is becoming more difficult due to more stringentregulations on the aromatics content in gasoline.

Para-xylene (p-xylene) is experiencing a market growth rate of demand.Consequently, the conversion of heavy aromatics to p-xylene provides avaluable product stream.

SUMMARY

Disclosed are methods and systems for production of xylenes.Specifically, disclosed are methods and systems for production ofxylenes from heavy aromatics.

In a first aspect, a method for producing mixed xylenes from a heavyreformate feed is provided. The method includes the steps of introducingthe heavy reformate feed to a feed exchanger to produce a hot feedstream, where the feed exchanger increases the temperature of the heavyreformate feed, where the heavy reformate includes aromatic hydrocarbonswith nine or more carbon atoms (C9+ aromatics), where the hydrogen feedincludes hydrogen gas, mixing the hot feed stream and a hydrogen feed toproduce a mixed feed, increasing a temperature of the mixed feed in afeed-effluent exchanger to produce a hot mixed feed, where a temperatureof the hot mixed feed is between 324 deg C. and 344 deg C., increasingthe temperature of the hot mixed feed in a feed fired heater to producea hot reactor feed, where a temperature of the hot reactor feed isbetween 380 deg C. and 400 deg C., introducing the hot reactor feed to adealkylation reactor, where the dealkylation reactor includes adealkylation catalyst, reacting the heavy reformate feed with thehydrogen gas in the presence of the dealkylation catalyst in thedealkylation reactor to produce a dealkylation effluent, where thedealkylation reactor is at a dealkylation temperature, where thedealkylation reactor is at a dealkylation pressure, where thedealkylation reactor has a liquid hourly space velocity, reducing atemperature of the dealkylation effluent in the feed-effluent exchangerto produce a cooled effluent stream, where a temperature of the cooledeffluent stream is between 115 deg C. and 145 deg C., reducing thetemperature of the cooled effluent in an effluent-separator exchanger toproduce an effluent stream, where a temperature of the effluent streamis between 80 deg C. and 110 deg C., reducing the temperature of theeffluent stream in an effluent cooler to produce a mixed effluentstream, where a temperature of the mixed effluent stream is between 38deg C. and 47 deg C., separating the mixed effluent stream in aneffluent separator to produce a produced hydrogen and a separatedeffluent, where the produced hydrogen includes hydrogen, increasing atemperature of the separated effluent in the effluent-separatorexchanger to produce a dealkylation splitter feed, where a temperatureof the dealkylation splitter feed is between 100 deg C. and 130 deg C.,introducing the dealkylation splitter feed to a splitter unit, where thedealkylation effluent includes light gases, toluene, benzene, mixedxylenes, and C9+ aromatics, separating the dealkylation effluent into alight gas product, a toluene stream, a benzene stream, a C9 aromaticsstream, a C10+ aromatics stream, and a mixed xylene stream in thesplitter unit, where the light gas stream includes light hydrocarbonsand hydrogen, where the toluene stream includes toluene, where thebenzene stream includes benzene, where the mixed xylene stream includesmixed xylenes, where the C9 stream includes C9 aromatics, where the C10+aromatics stream includes C10+ aromatics, mixing the toluene stream, theC9 aromatics stream, and a hydrogen stream in a mixer to produce a mixedtransalkylation feed, increasing a temperature of the mixedtransalkylation feed in a C9-effluent heater to produce a hottransalkylation feed, where a temperature of the hot transalkylationfeed is between 330 deg C. and 390 deg C., increasing the temperature ofthe hot transalkylation feed in a transalkylation fired heater toproduce a transalkylation feed, where a temperature of thetransalkylation feed is between 380 deg C. and 400 deg C., introducingthe transalkylation feed to a transalkylation reactor, where thetransalkylation reactor includes a transalkylation catalyst, where thehydrogen stream includes hydrogen gas, reacting the toluene stream andthe C9 aromatics stream in the presence of the transalkylation catalystto produce a transalkylation effluent, where the transalkylation reactoris at a transalkylation temperature, where the transalkylation reactoris at a transalkylation pressure, where the transalkylation reactor hasa liquid hourly space velocity, reducing a temperature of thetransalkylation effluent in the C9-effluent heater to produce a cooledtransalkylation effluent, where a temperature of the cooledtransalkylation effluent between 136 deg C. and 166 deg C., reducing thetemperature of the transalkylation effluent in aneffluent-transalkylation exchanger to produce a cooled effluent, where atemperature of the cooled effluent is between 83 deg C. and 103 deg C.,reducing the temperature of the cooled effluent in a transalkylationcooler to produce a cooled mixed effluent, where a temperature of thecooled mixed effluent is between 35 deg C. and 45 deg C., separating thecooled mixed effluent in a transalkylation separator to produce aseparated transalkylation effluent and a light gases stream, increasinga temperature of the separated transalkylation effluent in theeffluent-transalkylation exchanger to produce a transalkylation splitterfeed, where a temperature of the transalkylation splitter feed isbetween 105 deg C. and 125 deg C., introducing the transalkylationsplitter feed to the splitter unit, where the transalkylation effluentincludes light gases, toluene, benzene, mixed xylenes, and C9+aromatics, separating the transalkylation splitter feed in the splitterunit such that mixed xylenes in the transalkylation splitter feed exitthe splitter unit as part of the mixed xylene stream, reducing atemperature of the mixed xylene stream in the feed exchanger to producea cooled mixed stream, where a temperature of the cooled mixed stream isbetween 55 deg C. and 65 deg C., and reducing the temperature of thecooled mixed stream in a xylene cooler to produce a mixed xyleneproduct, where a temperature of the mixed xylene product is between 30deg C. and 50 deg C.

In certain aspects, the feed exchanger is a cross process exchanger,where the feed exchanger is configured to transfer heat from the mixedxylene stream to the heavy reformate feed. In certain aspects, thefeed-effluent exchanger is a cross process exchanger, where thefeed-effluent exchanger is configured to transfer heat from thedealkylation effluent to the mixed feed. In certain aspects, theeffluent-separator exchanger is a cross process exchanger, where theeffluent-separator exchanger is configured to transfer heat from thecooled effluent stream to the separated effluent. In certain aspects,the C9-effluent heater is a cross process exchanger, where theC9-effluent heater is configured to transfer heat from thetransalkylation effluent to the mixed transalkylation feed. In certainaspects, the effluent-transalkylation exchanger is a cross processexchanger, where the effluent-transalkylation exchanger is configured totransfer heat from the cooled transalkylation effluent to the separatedtransalkylation effluent. In certain aspects, the dealkylationtemperature is between 200 deg C. and 500 deg C., where the dealkylationpressure is between 5 bar and 40 bar, and where the liquid hourly spacevelocity in the dealkylation reactor is between 1 hr−1 and 10 hr−1. Incertain aspects, the transalkylation temperature is between 300 deg C.and 500 deg C., where the transalkylation pressure is between 10 bar and40 bar, where the liquid hourly space velocity in the transalkylationreactor is between 0.5 hr−1 and 6 hr−1.

In a second aspect, a method for producing mixed xylenes from a heavyreformate feed is provided. The method includes the steps of introducingthe heavy reformate feed to a feed exchanger to produce a hot feedstream, where the feed exchanger increases the temperature of the heavyreformate feed, where the heavy reformate includes aromatic hydrocarbonswith nine or more carbon atoms (C9+ aromatics), where the hydrogen feedincludes hydrogen gas, mixing the hot feed stream and a hydrogen feed toproduce a mixed feed, increasing a temperature of the mixed feed in afeed cross exchanger to produce a heated mixed feed, where a temperatureof the heated mixed feed is between 65 deg C. and 90 deg C., increasingthe temperature of the heated mixed feed in a feed-xylene exchanger toproduce a warm mixed feed, where a temperature of warm mixed feed isbetween 90 deg C. and 150 deg C., increasing the temperature of the warmmixed feed in a feed-effluent exchanger to produce a hot mixed feed,where a temperature of the hot mixed feed is between 324 deg C. and 344deg C., increasing the temperature of the hot mixed feed in a feed firedheater to produce a hot reactor feed, where a temperature of the hotreactor feed is between 380 deg C. and 400 deg C., introducing the hotreactor feed to a dealkylation reactor, where the dealkylation reactorincludes a dealkylation catalyst, reacting the heavy reformate feed withthe hydrogen gas in the presence of the dealkylation catalyst in thedealkylation reactor to produce a dealkylation effluent, where thedealkylation reactor is at a dealkylation temperature, where thedealkylation reactor is at a dealkylation pressure, where thedealkylation reactor has a liquid hourly space velocity, reducing atemperature of the dealkylation effluent in the feed-effluent exchangerto produce a cooled effluent stream, where a temperature of the cooledeffluent stream is between 115 deg C. and 145 deg C., reducing thetemperature of the cooled effluent in an effluent-separator exchanger toproduce an effluent stream, where the temperature of the effluent streamis between 80 deg C. and 110 deg C., reducing the temperature of theeffluent stream in the feed cross exchanger to produce a warm effluent,where a temperature of the warm effluent is between 65 deg C. and 80 degC., reducing the temperature of the warm effluent in an effluent coolerto produce a mixed effluent stream, where a temperature of the mixedeffluent stream is between 38 deg C. and 47 deg C., separating the mixedeffluent stream in an effluent separator to produce a produced hydrogenand a separated effluent, where the produced hydrogen includes hydrogen,increasing a temperature of the separated effluent in theeffluent-separator exchanger to produce a dealkylation splitter feed,where a temperature of the dealkylation splitter feed is between 100 degC. and 130 deg C., introducing the dealkylation splitter feed to asplitter unit, where the dealkylation effluent includes light gases,toluene, benzene, mixed xylenes, and C9+ aromatics, separating thedealkylation effluent into a light gas product, a toluene stream, abenzene stream, a C9 aromatics stream, a C10+ aromatics stream, and amixed xylene stream in the splitter unit, where the light gas streamincludes light hydrocarbons and hydrogen, where the toluene streamincludes toluene, where the benzene stream includes benzene, where themixed xylene stream includes mixed xylenes, where the C9 stream includesC9 aromatics, where the C10+ aromatics stream includes C10+ aromatics,mixing the toluene stream, the C9 aromatics stream, and a hydrogenstream in a mixer to produce a mixed transalkylation feed, increasing atemperature of the mixed transalkylation feed in a C9-effluent heater toproduce a hot transalkylation feed, where a temperature of the hottransalkylation feed is between 330 deg C. and 390 deg C., increasing atemperature of the hot transalkylation feed in a transalkylation firedheater to produce a transalkylation feed, where a temperature of thetransalkylation feed is between 380 deg C. and 400 deg C., introducingthe transalkylation feed to a transalkylation reactor, where thetransalkylation reactor includes a transalkylation catalyst, where thehydrogen stream includes hydrogen gas, reacting the toluene stream andthe C9 aromatics stream in the presence of the transalkylation catalystto produce a transalkylation effluent, where the transalkylation reactoris at a transalkylation temperature, where the transalkylation reactoris at a transalkylation pressure, where the transalkylation reactor hasa liquid hourly space velocity, reducing a temperature of thetransalkylation effluent in the C9-effluent heater to produce a cooledtransalkylation effluent, where a temperature of the cooledtransalkylation effluent between 136 deg C. and 166 deg C., reducing thetemperature of the cooled transalkylation effluent in aneffluent-transalkylation exchanger to produce a cooled effluent, where atemperature of the cooled effluent is between 83 deg C. and 103 deg C.,reducing the temperature of the cooled effluent in the feed exchanger toproduce a mixed effluent, where a temperature of the mixed effluent isbetween 45 deg C. and 78 deg C., reducing the temperature of the mixedeffluent in a transalkylation cooler to produce a cooled mixed effluent,where a temperature of the cooled mixed effluent is between 35 deg C.and 45 deg C., separating the cooled mixed effluent in a transalkylationseparator to produce a separated transalkylation effluent and a lightgases stream, increasing a temperature of the separated transalkylationeffluent in the effluent-transalkylation exchanger to produce atransalkylation splitter feed, where a temperature of thetransalkylation splitter feed is between 105 deg C. and 125 deg C.,introducing the transalkylation splitter feed to the splitter unit,where the transalkylation effluent includes light gases, toluene,benzene, mixed xylenes, and C9+ aromatics, separating thetransalkylation splitter feed in the splitter unit such that mixedxylenes in the transalkylation splitter feed exit the splitter unit aspart of the mixed xylene stream, reducing a temperature of the mixedxylene stream in the feed-xylene exchanger to produce a cooled xylenestream, where a temperature of the cooled xylene stream is between 55deg C. and 65 deg C., and reducing the temperature of the cooled xylenestream in a xylene cooler to produce a mixed xylene product, where atemperature of the mixed xylene product is between 30 deg C. and 50 degC.

In certain aspects, the feed exchanger is a cross process exchanger,where the feed exchanger is configured to transfer heat from the mixedxylene stream to the heavy reformate feed. In certain aspects, the feedcross exchanger is a cross process exchanger, where the feed crossexchanger is configured to transfer heat from the effluent stream to themixed feed. In certain aspects, the feed-xylene exchanger is a crossprocess exchanger, where the feed-xylene exchanger is configured totransfer heat from the mixed xylene stream to the heated mixed feed. Incertain aspects, the feed-effluent exchanger is a cross processexchanger, where the feed-effluent exchanger is configured to transferheat from the dealkylation effluent to the warm mixed feed.

BRIEF DESCRIPTION OF THE DRAWINGS

These and other features, aspects, and advantages of the scope willbecome better understood with regard to the following descriptions,claims, and accompanying drawings. It is to be noted, however, that thedrawings illustrate only several embodiments and are therefore not to beconsidered limiting of the scope as it can admit to other equallyeffective embodiments.

FIG. 1 provides a process diagram of an embodiment of the process.

FIG. 2 provides a process diagram of an embodiment of the process.

FIG. 3 provides a process diagram of an embodiment of the process.

FIG. 4 provides a process diagram of an embodiment of the process.

FIG. 5 provides a process diagram of a one-reactor system.

FIG. 6 provides a process diagram of an embodiment of the process.

FIG. 7 provides a process diagram of an embodiment of the process.

FIG. 8 provides a process diagram of an embodiment of the process.

FIG. 9 provides a process diagram of a process in the absence of asplitter unit between a dealkylation reactor and transalkylationreactor.

FIG. 10 provides a process diagram of an embodiment of the process withenergy optimization.

FIG. 11 provides a process diagram of an embodiment of the process withenergy optimization.

FIG. 12 provides a process diagram of an embodiment of the process withenergy optimization.

In the accompanying Figures, similar components or features, or both,may have a similar reference label.

DETAILED DESCRIPTION

While the scope of the apparatus and method will be described withseveral embodiments, it is understood that one of ordinary skill in therelevant art will appreciate that many examples, variations andalterations to the apparatus and methods described here are within thescope and spirit of the embodiments.

Accordingly, the embodiments described are set forth without any loss ofgenerality, and without imposing limitations, on the embodiments. Thoseof skill in the art understand that the scope includes all possiblecombinations and uses of particular features described in thespecification.

Described here are processes and systems of a three unit system for theproduction of mixed xylenes. A heavy reformate is introduced to adealkylation reactor. The dealkylation effluent from the dealkylationreactor is introduced to a splitter unit to separate the components ofthe dealkylation effluent. The toluene and C9+ aromatics from thesplitter unit are introduced to a transalkylation reactor. Optionally,the benzene can be introduced to the transalkylation reactor also. Thetransalkylation effluent from the transalkylation reactor is introducedto the splitter unit to separate the components of the transalkylationeffluent. The streams exiting the splitter unit include the componentsof the effluents from both the dealkylation reactor and thetransalkylation reactor.

Advantageously, the combination of a dealkylation reactor and a separatetransalkylation reactor increases the overall production of xylenes ascompared to a one-reactor system that contains both a dealkylationcatalyst and a transalkylation catalyst or a single catalyst capable ofboth dealkylation and transalkylation reactions. Advantageously,recycling the transalkylation effluent to the splitter unit increasesoverall yield because it minimizes the loss of xylene by reducing theproduction of benzene through disproportionation of toluene in thetransalkylation reactor. Advantageously, energy optimization allows forthe production of xylenes with optimized heat integration. There are twoprimary reactions that occur in the transalkylation reactor to formxylene, an equilibrium transalkylation reaction of toluene andtrimethylbenzene and an equilibrium disproportionation reaction oftoluene:CH₃C₆H₅+(CH₃)₃C₆H₃↔2(CH₃)₂C₆H₄  (Reaction 1)2CH₃C₆H₅↔C₆H₆+(CH₃)₂C₆H₄  (Reaction 2)

Recycling benzene will limit the production of benzene through Reaction2, reducing the consumption of toluene in Reaction 2 making more tolueneavailable for the production of xylene in Reaction 1.

As used throughout, a reference to “C” and a number refers to the numberof carbon atoms in a hydrocarbon. For example, C1 refers to ahydrocarbon with one carbon atom and C6 refers to a hydrocarbon with sixcarbon atoms.

As used throughout, “C9 aromatics” refers to aromatic hydrocarbons withnine carbon atoms. Examples of C9 aromatic hydrocarbons includemethylethylbenzene, trimethylbenzene, and propylbenzene.

As used throughout, “trimethylbenzene” includes each of the isomers oftrimethylbenzene: hemellitene, pseudocumene, and mesitylene.

As used throughout, “C10+ aromatics” refers to aromatic hydrocarbonswith ten carbon atoms and aromatics with more than ten carbon atoms,such as an aromatic hydrocarbon with eleven carbon atoms.

As used throughout, “C9+ aromatics” refers to the group of C9 aromaticsand C10+ aromatics.

As used throughout, “mixed xylenes” refers to one or more of para-xylene(p-xylene), meta-xylene (m-xylene), and ortho-xylene (o-xylene).

As used throughout, “dealkylation reaction” refers to a reaction thatresults in the removal of an alkyl group from one or more of thereactants.

As used throughout, “transalkylation reaction” refers to a reaction thatresults in the transfer of an alkyl group from one or compound toanother.

As used throughout, “light hydrocarbons” refers to one or more ofalkanes, including methane, ethane, propane, butanes, pentanes, alkenes,and trace amounts of naphthenes, such as cyclopentane, cyclohexane.

As used throughout, “light gases” refers to one or more of lighthydrocarbons, hydrogen, and air.

Referring to FIG. 1 an embodiment of the process for producing mixedxylenes in provided. Heavy reformate feed 100 is introduced todealkylation reactor 10 along with hydrogen feed 105. Heavy reformatefeed 100 can include toluene, mixed xylenes, C9 aromatics, and C9+aromatics. In at least one embodiment, heavy reformate feed 100 caninclude trace amounts of C8+ naphthenes and C10+ naphthylenes, includingthe alkyl derivatives of the same. In at least one embodiment, heavyreformate feed 100 can contain between 0 wt % and 10 wt % mixed xylenesand between 60 wt % and 100 wt % C9+ aromatics. In at least oneembodiment, heavy reformate feed 100 can contain between 0 wt % and 60wt % toluene. In at least one embodiment, heavy reformate feed 100 cancontain between 0 wt % and 10 wt % mixed xylenes, between 0 wt % and 60wt % toluene, and between 60 wt % and 100 wt % C9+ aromatics. In atleast one embodiment, heavy reformate feed 100 contains between 60 wt %and 100 wt % C9 aromatics and is in the absence of C10+ aromatics.

Hydrogen feed 105 can be any stream containing hydrogen gas. Hydrogenfeed 105 can be a stream of pure hydrogen from a fresh hydrogen source.In at least one embodiment described with reference to FIG. 2, hydrogengas can be recovered from the process in gas separator 40 as producedhydrogen 145, which can be divided such that a portion of producedhydrogen 145 can be recycled as hydrogen feed 105 and introduced todealkylation reactor 10. In at least one embodiment, hydrogen feed 105can be from a hydrogen source in a refinery and can contain lighthydrocarbons.

Returning to FIG. 1, dealkylation reactor 10 can be any type of reactorcapable of containing and supporting a dealkylation reaction.Dealkylation reactor 10 can be a fixed bed reactor or a fluidized bedreactor. The dealkylation temperature in dealkylation reactor 10 can bebetween 200 degrees Celsius (deg C.) and 500 deg C. The dealkylationpressure in dealkylation reactor 10 can be between 5 bar (500 kilopascal(kPa)) and 40 bar (4000 kPa). The liquid hourly space velocity (LHSV)can be between 1 per hour (hr⁻¹) and 10 hr⁻¹.

Dealkylation reactor 10 can include a dealkylation catalyst. Thedealkylation catalyst can include any catalysts capable of catalyzingdealkylation reactions. Examples of dealkylation catalyst can includebifunctional catalysts such as those described in U.S. Pat. No.9,000,247. The dealkylation catalyst can be selected to selectivelyconvert one or more of the C9+ aromatics over the others in dealkylationreactions. Dealkylation reactions can convert C9+ aromatics to toluene,benzene, mixed xylenes, and light gases; and can convert C10+ aromaticsto C9+ aromatics. Reactions in dealkylation reactor 10 can removemethyl, ethyl, propyl, butyl and pentyl groups, and their isomers,attached to C10+ aromatics. In at least one embodiment, a dealkylationcatalyst can be selected to convert more than 97.5 wt % of themethylethylbenzene to toluene. In at least one embodiment, the overallconversion of C9+ aromatics can be above 98 wt % due to conversion of C9aromatics and the removal of methyl, ethyl, propyl, butyl and pentylgroups attached to C10+ aromatics. Dealkylation effluent 110 can containmixed xylenes, toluene, benzene, light gases, and C9+ aromatics.

In at least one embodiment, where hydrogen feed 105 is introduced todealkylation reactor 10, dealkylation reactor 10 is a fixed bed reactorand the light gases produced in dealkylation effluent 110 containalkanes. In at least one embodiment, dealkylation reactor 10 is in theabsence of a hydrogen stream (not shown), dealkylation reactor 10 is afluidized bed reactor and the light gases produced in dealkylationeffluent 110 contain alkenes.

Dealkylation effluent 110 is introduced to splitter unit 20.

Splitter unit 20 can be any type of separation unit capable ofseparating a stream into its component parts. In at least oneembodiment, splitter unit 20 can be one splitter column designed toseparate the feed stream into multiple split streams. In at least oneembodiment, splitter unit 20 can be multiple splitter columns in seriesdesigned to separate one component from the feed stream. In at least oneembodiment, splitter unit 20 can be one or more distillation units. Inat least one embodiment, where splitter unit 20 is multiple splittercolumns, splitter unit 20 includes five splitter columns: a first columnoperates at a pressure of between 4 bar gauge (barg) and 6 barg and atemperature between 100 deg C. and 200 deg C. to separate light gasesfrom the first column feed to produce light gas stream 122 and a firstcolumn effluent; a second column operates at a pressure of between 0.6barg and 1.5 barg and a temperature between 100 deg C. and 170 deg C. toseparate benzene and toluene from the first column effluent to produce abenzene/toluene stream and a second column effluent; a third columnoperates at a pressure of between 0.3 barg and 0.9 barg and atemperature between 70 deg C. and 150 deg C. to separate benzene fromthe benzene/toluene stream to produce benzene stream 126 and to separatetoluene from the benzene toluene stream to produce toluene stream 124; afourth column operates at a pressure of between 0.3 barg and 2 barg anda temperature between 120 deg C. and 210 deg C. to separate xylenes fromthe second column effluent to produce mixed xylene stream 120 and a C9+aromatics stream; and a fifth column operates at a pressure of between0.5 barg and 3 barg and a temperature of between 150 deg C. and 250 degC. to separate C9 aromatics from the C9+ aromatics stream to produce C9aromatics stream 128 and to separate C10+ aromatics from the C9+aromatics stream to produce C10+ aromatics stream 132. In at least oneembodiment, where splitter unit 20 is multiple splitter columns,splitter unit 20 can be in the absence of a column to separate C9aromatics from C10+ aromatics, such that the column to separate xylenesproduces the xylene stream and a C9+ stream. The C9+ stream can beintroduced to the transalkylation reactor. In at least one embodiment,where splitter unit 20 is multiple splitter columns, splitter unit 20can be in the absence of a column to separate benzene/toluene stream. Itcan be understood by one of skill in the art that splitter unit 20 canbe designed to operate at a temperature and pressure to produce thedesired streams. In at least one embodiment, where splitter unit 20 isone distillation column, the distillation column can include multiplesections in one vessel, where each section has the operating conditionscorresponding to each of the separate columns described in thisparagraph.

Splitter unit 20 separates the components to produce mixed xylene stream120, light gas stream 122, toluene stream 124, benzene stream 126, C9aromatics stream 128, and C10+ aromatics stream 132. Mixed xylene stream120 contains mixed xylenes. Light gas stream 122 contains light gases.Toluene stream 124 contains toluene. Benzene stream 126 containsbenzene. C9 aromatics stream 128 contains C9 aromatics, including C9aromatics formed in dealkylation reactor 10 and unreacted C9 aromaticsfrom heavy reformate feed 100. C10+ aromatics stream 132 contains C10+aromatics, including C10+ aromatics formed in dealkylation reactor 10and unreacted C10+ aromatics from heavy reformate feed 100. In at leastone embodiment, C10+ aromatics stream 132 can be purged from the system.In at least one embodiment, C10+ aromatics stream 132 can be introducedto dealkylation reactor 10 for further processing to increase theconversion of C10+ aromatics.

Advantageously, the separation and removal of mixed xylenes in thesplitter unit increases production of mixed xylenes in thetransalkylation reactor. The absence of mixed xylenes in the feed totransalkylation reactor 30 drives the thermodynamic equilibrium ofReaction 1 towards xylene production in transalkylation reactor 30.

Toluene stream 124 and C9 aromatics stream 128 are introduced totransalkylation reactor 30 along with hydrogen stream 135. Hydrogenstream 135 can be any stream containing hydrogen gas. Hydrogen stream135 can be a stream of pure hydrogen from a fresh hydrogen source. In atleast one embodiment described with reference to FIG. 2, producedhydrogen 145 can be divided such that a portion of produced hydrogen 145can be recycled as hydrogen feed 105 and introduced to dealkylationreactor 10 and a second portion of produced hydrogen can be recycled ashydrogen stream 135 and introduced to transalkylation reactor 30.

Transalkylation reactor 30 can be a fixed bed reactor or a fluidized bedreactor. The transalkylation temperature in transalkylation reactor 30can be between 300 deg C. and 500 deg C. The transalkylation pressure intransalkylation reactor 30 can be between 10 bar (1000 kPa) and 40 bar(4000 kPa). The liquid hourly space velocity (LHSV) can be between 0.5hr⁻¹ and 6 hr⁻¹. The operating conditions can be set to maximize theproduction of xylenes. The temperature can have a greater influence onthe transalkylation reaction than pressure. It is understood that highertemperatures, higher pressures, and lower LHSV favor transalkylationreactions, while higher temperatures can lead to catalyst deactivationand therefore, the operating conditions must be balanced to maximizeproduction and minimize catalyst deactivation.

Transalkylation reactor 30 can include a transalkylation catalyst. Thetransalkylation catalyst can include any catalyst capable of catalyzingtransalkylation reactions. Examples of transalkylation catalysts includebifunctional catalysts as described in U.S. Pat. No. 9,000,247. Thetransalkylation catalyst can be selected to selectively convert one ormore of the C9+ aromatics over the others in transalkylation reactions.In at least one embodiment, the transalkylation catalyst can be selectedto selectively convert trimethylbenzenes to mixed xylenes.Transalkylation reactions can occur to convert C9+ aromatics to toluene,benzene, mixed xylenes, and light gases. Transalkylation effluent 130contains mixed xylenes, toluene, benzene, light gases, and C9+aromatics.

In at least one embodiment, with reference to FIG. 3, benzene stream 126can be introduced to transalkylation reactor 30. In at least oneembodiment, a slip stream can be removed from benzene stream 126 asbenzene product 326. The volume of benzene stream 126 introduced totransalkylation reactor 30 can be determined based on the reactionconditions desired in transalkylation reactor 30. In at least oneembodiment, the volume of benzene stream 126 introduced totransalkylation reactor 30 can be controlled by the flow rate of benzeneproduct 326. Adding benzene from benzene stream 126 to transalkylationreactor 30 can minimize the production of benzene through Reaction 2 andincrease the production of mixed xylenes through Reaction 1.

Transalkylation reactor 30 produces transalkylation effluent 130.Transalkylation effluent 130 can contain mixed xylenes, toluene,benzene, light gases, and C9+ aromatics, including C9+ aromatics formedin transalkylation reactor 30 and unreacted C9+ aromatics from heavyreformate feed 100.

Transalkylation effluent 130 can be introduced to splitter unit 20.Transalkylation effluent 130 is separated in splitter unit 20 and thecomponent parts form part of mixed xylene stream 120, light gas stream122, toluene stream 124, benzene stream 126, C9 aromatics stream 128,and C10+ aromatics stream 132.

The overall yield of mixed xylenes in mixed xylene stream 120 can bebetween 30 wt % and 89 wt %. In at least one embodiment, the overallyield of mixed xylenes in mixed xylene stream 120 is 80 wt %. Theoverall yield of toluene can be between 0 wt % and 20 wt % andalternately between 5 wt % and 20 wt %. The overall yield of benzene canbe between 0 wt % and 10 wt % and alternately between 1 wt % and 10 wt%. Mixed xylene stream 120 can be introduced to an isomerization unit ora crystallization unit to convert m-xylene and o-xylene to p-xylene.

Referring to FIG. 2, an embodiment of the process to produce mixedxylenes is provided. Light gas stream 122 is introduced to gas separator40. Gas separator 40 can be any type of separation unit capable ofseparating hydrogen from a stream of gases. In at least one embodiment,gas separator 40 is a pressure swing adsorption unit. In at least oneembodiment, gas separator 40 is a hydrogen membrane separation unit. Gasseparator 40 can separate light gas stream 122 into light gas product140 and produced hydrogen 145. Produced hydrogen 145 can be split tocreate hydrogen feed 105 and hydrogen stream 135. Light gas product 140contains light hydrocarbons. Produced hydrogen 145 contains hydrogen.Light gas product 140 can be purged to the atmosphere, used as a sourcefuel, or sent for further processing.

Referring to FIG. 4, an embodiment of the process to produce mixedxylenes is provided with reference to FIG. 1. Added aromatic stream 500is introduced to transalkylation reactor 30. Added aromatic stream 500can include toluene, benzene, or combinations of the same. In at leastone embodiment, added aromatic stream 500 includes toluene. The flowrate of added aromatic stream 500 can be at a volume to provide surplustoluene to increase conversion of trimethylbenzene in the reactionbetween toluene and trimethylbenzene present in C9 aromatics stream 128.Added aromatic stream 500 can be used to increase the methyl group toaromatic ratio to 2, which can increase the conversion of C9 aromaticsto xylenes. In at least one embodiment, dealkylation reactor 10 is inthe absence of an added aromatic stream.

In at least one embodiment, the dealkylation reactor and thetransalkylation reactor can be housed in one vessel, where the tworeactor stages are physically separate from each other with no minglingof the internal gases. The effluent from the dealkylation reactor stagecan exit the vessel and enter a splitter unit where the benzene stream,toluene stream, and C9 aromatics stream can be separated and thenreintroduced to the vessel in the transalkylation reactor stage.

Advantageously, the position of the dealkylation reactor upstream of thetransalkylation produces toluene not present in the heavy reformatefeed, toluene is a reactant in transalkylation reactions to producexylene, thus a process with the dealkylation reactor upstream of thetransalkylation increases xylene production. Advantageously, theposition of the dealkylation reactor upstream of the transalkylationreactor reduces the amount of C9 aromatics and C10+ aromatics beingintroduced to the transalkylation reactor.

Both the dealkylation reactor and the transalkylation reactor are in theabsence of methanol and in the absence of methylation reactions, whichare irreversible reactions that add a methyl group to a compound. In atleast one embodiment, the heavy reformate feed is in the absence ofethylbenzene.

Heat exchangers and separators can be included in the process to producemixed xylenes. Advantageously, cross-exchangers can be used to optimizeenergy consumption across the entire system and process. An embodimentof energy optimization of the process to produce mixed xylenes isdescribed with reference to FIG. 10. The energy optimization of theprocess to produce mixed xylenes incorporates cross process exchangers,which can be any type of heat exchanger capable of transferring heatfrom one process stream to a separate process stream. The cross processexchangers can include parallel-flow exchangers, counter-flowexchangers, and cross-flow exchangers. Examples of cross processexchangers can include shell and tube heat exchangers, plate heatexchangers, spiral heat exchangers, and combinations of the same.Referring to FIG. 10, feed exchanger 10-1, feed-effluent exchanger 10-2,effluent-separator exchanger 20-3, C9-effluent heater 30-2, andeffluent-transalkylation exchanger 20-6 are cross process exchangers.Referring to FIG. 11, feed cross exchanger 10-5 feed-xylene exchanger10-6 are cross process exchangers. Advantageously, maximizing the numberof cross process exchangers reduces the energy input required for thesystem and optimizes the overall energy consumption. Other sources ofheat can include fired heaters, which can be any type of direct heatexchanger. Referring to FIG. 10, feed fired heater 10-3 andtransalkylation fired heater 30-3 can be fired heaters. Other units toremove heat from process streams can include heat exchangers, which canbe any type of heat exchanger where a non-process stream fluid medium isused to remove heat from a process stream. Examples of heat exchangerscan include shell and tube heat exchangers, plate heat exchangers,spiral heat exchangers, and combinations of the same. Referring to FIG.10, xylene cooler 10-4, effluent cooler 20-1, and transalkylation cooler20-4 are heat exchangers where the heat is removed using a non-processstream fluid medium.

Heavy reformate 100 can be heated in feed exchanger 10-1 to produce hotfeed stream 200. The temperature of hot feed stream 200 can be between105 deg C. and 125 deg C. Hot feed stream 200 and hydrogen feed 105 canbe mixed to produce mixed feed 205. Mixed feed 205 can be heated infeed-effluent exchanger 10-2 to produce hot mixed feed 210. Hot mixedfeed 210 can have a temperature between 324 deg C. and 344 deg C. Hotmixed feed 210 can be heated in feed fired heater 10-3 to produce hotreactor feed 215. Hot reactor feed 215 can be at a temperature between380 deg C. and 400 deg C. Hot reactor feed 215 can be reacted indealkylation reactor 10 to produce dealkylation effluent 110.Dealkylation effluent 110 can be at a temperature between 350 deg C. and420 deg C. Dealkylation effluent 110 can be cooled in feed-effluentexchanger 10-2 to produce cooled effluent stream 220. Cooled effluentstream 220 can be at a temperature between 115 deg C. and 145 deg C.

Cooled effluent stream 220 can be cooled in effluent-separator exchanger20-3 to produce effluent stream 225. Effluent stream 225 can be at atemperature between 80 deg C. and 110 deg C. Effluent stream 225 can becooled in effluent cooler 20-1 to produced mixed effluent stream 230.Mixed effluent stream 230 can be at a temperature between 38 deg C. and47 deg C. Hydrogen in mixed effluent stream 230 can be separated ineffluent separator 20-2 to produce produced hydrogen 145 and separatedeffluent 240. Separated effluent 240 can be heated in effluent-separatorexchanger 20-3 to produce dealkylation splitter feed 247. Dealkylationsplitter feed 247 can be at a temperature in the range of 100 deg C. and130 deg C.

Dealkylation splitter feed 247 can be separated in splitter unit 20 toproduce light gas product 140, toluene stream 124, benzene stream 126,C9 aromatics stream 128, C10+ aromatics stream 132, and mixed xylenestream 120. Toluene stream 124, C9 aromatics stream 128, and hydrogenstream 135 can be mixed in mixer 30-1 to produce mixed transalkylationfeed 250. Mixed transalkylation feed 250 can be heated in C9-effluentheater 30-2 to produce hot transalkylation feed 255. Hot transalkylationfeed 255 can be at a temperature between 330 deg C. and 390 deg C. Hottransalkylation feed 255 can be heated in transalkylation fired heater30-3 to produce transalkylation feed 260. Transalkylation feed 260 canbe at a temperature between 380 deg C. and 400 deg C.

Transalkylation feed 260 can be reacted in transalkylation reactor 30 toproduce transalkylation effluent 130. Transalkylation effluent 130 canbe cooled in transalkylation cooler 20-4 to produce cooledtransalkylation effluent 265. Cooled transalkylation effluent 265 can beat a temperature between 136 deg C. and 166 deg C. Cooledtransalkylation effluent 265 can be cooled in effluent-transalkylationexchanger 20-6 to produce cooled effluent 270. Cooled effluent 270 canbe at a temperature between 83 deg C. and 103 deg C. Cooled effluent 270can be cooled in transalkylation cooler 20-4 to produce cooled mixedeffluent 275. Cooled mixed effluent 275 can be at a temperature between35 deg C. and 45 deg C. Light gases stream 235 can be separated intransalkylation separator 20-5 to produce separated transalkylationeffluent 280. Light gases stream 235 can include light gases. Separatedtransalkylation effluent 280 can be heated in effluent-transalkylationexchanger 20-6 to produce transalkylation splitter feed 285.Transalkylation splitter feed 285 can be at a temperature between 105deg C. and 125 deg C.

Mixed xylene stream 120 can be cooled in feed exchanger 10-1 to producecooled mixed stream 290. Cooled mixed stream 290 can be at a temperaturebetween 55 deg C. and 65 deg C. Cooled mixed stream 290 can be cooled inxylene cooler 10-4 to produce mixed xylene product 295. The temperatureof mixed xylene product 295 can be between 30 deg C. and 50 deg C.

Referring to FIG. 11, an alternate embodiment of the energy optimizationof the process to produce mixed xylenes is described and can beunderstood with reference to FIG. 10. Additional cross processexchangers are included. Mixed feed 205 can be heated in feed crossexchanger 10-5 to produce heated mixed feed 207. Heated mixed feed 207can be at a temperature between 65 deg C. and 90 deg C. Heated mixedfeed 207 can be heated in feed-xylene exchanger 10-6 to produce warmmixed feed 209. Warm mixed feed 209 can be at a temperature between 90deg C. and 150 deg C. Warm mixed feed 209 can be heated in feed-effluentexchanger 10-2 to produce hot mixed feed 210.

Effluent stream 225 can be cooled in feed cross exchanger 10-5 toproduce warm effluent 227. The temperature of warm effluent 227 can bein the range between 65 deg C. and 80 deg C. Warm effluent 227 can becooled in effluent cooler 20-1 to produce mixed effluent stream 230.

Cooled effluent 270 can be cooled in feed exchanger 10-1 to producemixed effluent 272. The temperature of mixed effluent 272 can be in therange between 45 deg C. and 78 deg C. Mixed effluent 272 can be cooledin transalkylation cooler 20-4 to produce cooled mixed effluent 275.Mixed xylenes 120 can be cooled in feed-xylene exchanger 10-6 to producecooled xylene stream 292. Cooled xylene stream 292 can be at atemperature between 80 deg C. and 100 deg C. Cooled xylene stream 292can be cooled in xylene cooler 10-4 to produce mixed xylene product 295.

EXAMPLES

The following examples were carried out in laboratory equipment.

Example 1

Example 1 provides an analysis of dealkylation reactor 10 with referenceto FIG. 2. Heavy reformate feed 100 had the composition in Table 1.Hydrogen feed 105 was recycled from produced hydrogen 145 after beingrecovered from gas separator 40.

TABLE 1 Composition of heavy reformate feed 100 Component Composition,wt % Ethylbenzene 0.0498 Mixed xylenes 5.1789 C9 aromatics total 80.1502Trimethylbenzene 56.5475 Methylethylbenzene 21.0869 Propylbenzene 2.5158C10+ aromatics 14.6211

Dealkylation reactor 10 was at a temperature of 400 deg C. and apressure of 30 bar (3000 kPa). The weight hourly space velocity (whsv)was 4.2 per hour (hr⁻¹). The ratio of hydrogen gas (H₂) to hydrocarbonswas 4:1 (mol/mol). The catalyst was a ZSM-5 catalyst designed fordealkylation reactions to selectively convert methylethylbenzenes totoluene, benzene, and light alkanes. The composition of dealkylationeffluent 110 is shown in Table 2.

TABLE 2 Composition of dealkylation effluent 110 Component Composition,wt % Light hydrocarbons 7.00 Benzene 2.49 Toluene 16.26 Ethylbenzene0.04 Mixed xylenes 16.49 C9 aromatics total 50.65 Trimethylbenzene 50.39Methylethylbenzene 0.26 Propylbenzene 0 C10+ aromatics 7.08

The conversion of methylethylbenzene in dealkylation reactor 10 was 98.8wt %. The conversion of trimethylbenzene in dealkylation reactor 10 was10.9 wt %.

Example 2

Example 2 provides an analysis of transalkylation reactor 30 withreference to FIG. 2. The combined feed to transalkylation reactor 30 hadthe composition in Table 3.

TABLE 3 Composition of feed to transalkylation reactor 30 ComponentComposition, wt % Toluene 50 Trimethylbenzene 50

Transalkylation reactor 30 was at a temperature of 400 deg C. and apressure of 30 bar (3000 kPa). The whsv was 4.2 hr⁻¹. The ratio ofhydrogen gas (H₂) to hydrocarbons is 4:1 (mol/mol). The catalyst was atransalkylation catalyst with a zeolite. The composition oftransalkylation effluent 130 is shown in Table 4.

TABLE 4 Composition of transalkylation effluent 130 ComponentComposition, wt % Light hydrocarbons 8.4 Benzene 3.9 Toluene 22.1Ethylbenzene 0.3 Mixed xylenes 37 C9 aromatics total 20.8Trimethylbenzene 19.9 Methylethylbenzene 0.9 Propylbenzene 0 C10+aromatics 6.3

The conversion of trimethylbenzene in transalkylation reactor 30 was 56wt %. The conversion of toluene in transalkylation reactor 30 was 52 wt%.

Example 3

Example 3 was a comparative example of a one-reactor system, wheredealkylation reactions and transalkylation reactions occur in the samereactor, coupled with a splitter unit described with reference to FIG. 5and FIG. 2. Heavy reformate feed 100, having the composition describedin Table 5, was introduced to transalkylation-dealkylation reactor 60along with hydrogen feed 105. Hydrogen feed 105 was simulated as a feedfrom a hydrogen source in a refinery containing only hydrogen.

TABLE 5 Composition of heavy reformate feed 100 Composition, kilogramper hour (kg/hr) Heavy Reformate Hydrogen Produced Component Feed 100Feed 105 Hydrogen 145 Hydrogen 0 20 16.5 Light hydrocarbons 0 0 0Benzene 0 0 0 Toluene 0 0 0 Ethylbenzene 0 0 0 Mixed xylenes 51 0 0 C9aromatics total 835 0 0 Trimethylbenzene 592 — — Methylethylbenzene 213— — Propylbenzene 30 — — C10+ aromatics 114 0 0

Transalkylation-dealkylation reactor 60 was operated at a temperature of400 deg C., a pressure of 20 bar, a whsv of 4.2 hr⁻¹, and a hydrogen tohydrocarbon ratio of 4:1. The catalyst was a catalyst was a 40% beta and60% MCM-41 catalyst that can facilitate both transalkylation anddealkylation reactions.

One-reactor effluent 610 was introduced to splitter unit 20. Splitterunit 20 operated to separate one-reactor effluent 610 into its componentparts, as shown in Table 6. Light product 622 was introduced to gasseparator 40 which separated hydrogen from light hydrocarbons to produceproduced hydrogen 145 and gas product 640 containing light hydrocarbons.

TABLE 6 Composition of Streams Exiting Splitter Unit 20 in Example 3Composition, kg/hr Light C9 Aro- C10+ Aro- gas Benzene Toluene Xylenematics matics Component 622 626 624 620 628 632 Hydrogen 16.5 0 0 0 0 0Light hydro- 20.6 0 0 0 0 0 carbons Benzene 0 12.0 0 0 0 0 Toluene 0 0113.6 0 0 0 Ethylbenzene 0 0 0 3.6 0 0 Mixed 0 0 0 339.7 0 0 xylenes C9aromatics 0 0 0 0 366.7 0 total Trimethyl- — — — — 324.9 — benzeneMethylethyl- — — — — 41.7 — benzene Propylben- — — — — 0 — zene C10+ 0 00 0 0 147.3 aromatics

The mixed xylene yield was 34 wt %, which was in the range of xyleneyield for a one-reactor system, of between 32 wt % and 35 wt %. In aone-reactor system, the production of xylene is limited by thethermodynamic equilibrium, as shown in Reaction 1. The conversion ofmethylethylbenzene was 80%, which falls within then typical range ofmethylethylbenzene conversion in a one-reactor system of between 80 wt %and 92 wt %. The conversion of trimethylbenzene was 45%, which wasslightly outside of the typical range of trimethylbenzene conversion ofaround 50 wt %.

Example 4

Example 4 was a simulation of the process to produce mixed xylenes withreference to FIG. 6 and FIG. 2. Heavy reformate feed 100, having thecomposition in Table 7, is introduced to dealkylation reactor 10 alongwith hydrogen feed 105. The flow rate of hydrogen feed 105 was 138.6kg/hr, with 66.5 kg/hr of hydrogen gas and 72.0 kg/hr lighthydrocarbons.

TABLE 7 Composition of heavy reformate feed 100 Component Composition,kg/hr Composition, wt % Mass Flow 1000.0 100 Hydrogen 0 0.0 Light gases0 0.0 Benzene 0 0.0 Toluene 0 0.0 Ethylbenzene 0.5 0.0 Mixed xylenes51.8 5.2 m-xylene 31.8 3.2 o-xylene 10.0 1.0 p-xylene 10.0 1.0 C9aromatics total 801.6 80.2 Trimethylbenzene 565.5 56.5Methylethylbenzene 210.9 21.1 Propylbenzene 25.2 2.5 C10+ aromatics146.2 14.6

Dealkylation reactor 10 was at a temperature of 400 deg C. and apressure of 30 bar (3000 kPa). The whsv was 4.2 h⁻¹. The ratio ofhydrogen gas (H₂) to hydrocarbons was 4:1 (mol/mol). The catalyst was a3-dimensional zeolite-based dealkylation catalyst. The composition ofdealkylation effluent 110 is shown in Table 8.

TABLE 8 Composition of dealkylation effluent 110 Composition, wt %Component Composition, kg/hr without hydrogen gas Mass Flow 1138.6 —Hydrogen 63.0 — Light gases 106.5 9.9 Benzene 26.8 2.5 Toluene 174.916.3 Ethylbenzene 0.4 0.0 Mixed xylenes 177.5 16.5 m-xylene 102.2 9.5o-xylene 39.9 3.7 p-xylene 35.4 3.3 C9 aromatics total 506.4 47.1Trimethylbenzene 503.8 46.8 Methylethylbenzene 2.5 0.2 Propylbenzene 0.00.0 C10+ aromatics 83.1 7.7

Dealkylation effluent 110 was introduced to splitter unit 20 whichseparated dealkylation effluent 110 into its component parts. Light gasstream 122 was introduced to gas separator 40 to produce light gasproduct 140 and produced hydrogen 145. Produced hydrogen 145 was splitto produce hydrogen slipstream 245 and hydrogen stream 135. Thecomposition and flow rates are shown in Table 9.

TABLE 9 Composition of streams Composition, kg/hr Stream Stream StreamStream Stream Component 122 140 145 135 245 Mass Flow 407.6 222.1 185.5126.9 58.6 Hydrogen 185.5 0.0 185.5 126.9 58.6 Light gases 222.1 222.10.0 0.0 0.0 Benzene 0.0 0.0 0.0 0.0 0.0 Toluene 0.0 0.0 0.0 0.0 0.0Ethylbenzene 0.0 0.0 0.0 0.0 0.0 Mixed xylenes 0.0 0.0 0.0 0.0 0.0m-xylene — — — — — o-xylene — — — — — p-xylene — — — — — C9 aromaticstotal 0.0 0.0 0.0 0.0 0.0 Trimethylbenzene — — — — — Methylethylbenzene— — — — — Propylbenzene — — — — — C10+ aromatics 0.0 0.0 0.0 0.0 0.0

Benzene stream 126, toluene stream 124, and C9 aromatics stream 128 wereintroduced to transalkylation reactor 30 along with added aromaticstream 500 and hydrogen stream 135. The flow rate of added aromaticstream 500 was 70.0 kg/hr of pure toluene which creates a surplus oftoluene in transalkylation reactor 30. Transalkylation reactor 30 was ata temperature of 400 deg C. and a pressure of 30 bar (3000 kPa). Thewhsv was 4.2 h⁻¹. The ratio of hydrogen gas (H₂) to hydrocarbons is 4:1(mol/mol). The catalyst was a 1-dimensional zeolite-basedtransalkylation catalyst. The transalkylation catalyst was not the sameas the dealkylation catalyst. The composition of various streams areshown in Table 10.

TABLE 10 Composition of Streams Composition, kg/hr (wt % calculated withno hydrogen gas) Component Stream 120 Stream 124 Stream 126 Stream 128Stream 132 Stream 130 Mass Flow 844.8 537.4 62.8 1003.2 83.1 1800.3Hydrogen  0.0  0.0  0.0   0.0  0.0  122.4 Light hydrocarbons  0.0  0.0 0.0   0.0  0.0  115.6 Benzene  0.0  0.0 62.8 (100)   0.0  0.0  36.1(6.9) Toluene  0.0 537.4 (100)  0.0   0.0  0.0  362.5 (21.6)Ethylbenzene  30.3 (3.6)  0.0  0.0   0.0  0.0  29.9 (1.8) Mixed xylenes814.5 (96.4)  0.0  0.0   0.0  0.0  637.1 (38.0) m-xylene 469.0 (55.5) —— — —  366.8 (21.9) o-xylene 183.1 (21.7) — — — —  143.2 (8.5) p-xylene162.4 (19.2) — — — —  127.0 (7.6) C9 aromatics total  0.0  0.0  0.01003.2 (100)  0.0  496.8 (29.6) Trimethylbenzene — — —  998.7 (99.5) — 494.8 (29.5) Methylethylbenzene — — —   4.5 (0.5) —   2.0 (0.1)Propylbenzene — — —   0.0 (0.0) —   0.0 C10+ aromatics  0.0  0.0  0.0  0.0 83.1 (100)   0.0

The production of mixed xylenes in Example 4 was 814.5 kg/hr. Theoverall conversion of trimethylbenzene and methylethylbenzene was 100%.

Example 5

Example 5 was a simulation of the process to produce mixed xylenes withreference to FIG. 7. Heavy reformate feed 100, having the composition inTable 11, was introduced to dealkylation reactor 10 along with hydrogenfeed 105. The flow rate of hydrogen feed 105 was 138.6 kg/hr with 66.5kg/hr hydrogen gas and 72.0 kg/hr light hydrocarbons.

TABLE 11 Composition of heavy reformate feed 100 Component Composition,kg/hr Composition, wt % Mass Flow 1000.0 100 Hydrogen 0 0.0 Light gases0 0.0 Benzene 0 0.0 Toluene 0 0.0 Ethylbenzene 0.5 0.0 Mixed xylenes51.8 5.2 m-xylene 31.8 3.2 o-xylene 10.0 1.0 p-xylene 10.0 1.0 C9aromatics total 801.6 80.2 Trimethylbenzene 565.5 56.5Methylethylbenzene 210.9 21.1 Propylbenzene 25.2 2.5 C10+ aromatics146.2 14.6

Dealkylation reactor 10 was at a temperature of 400 deg C. and apressure of 30 bar (3000 kPa). The whsv was 4.2 hr⁻¹. The ratio ofhydrogen gas (H₂) to hydrocarbons was 4:1 (mol/mol). The catalyst was a3-dimensional zeolite-based dealkylation catalyst. The composition ofdealkylation effluent 110 is shown in Table 12.

TABLE 12 Composition of dealkylation effluent 110 Composition, wt %calculated without Component Composition, kg/hr hydrogen gas Mass Flow1138.6 — Hydrogen 63.0 — Light gases 106.5 9.9 Benzene 26.8 2.5 Toluene174.9 16.3 Ethylbenzene 0.4 0.0 Mixed xylenes 177.5 16.5 m-xylene 102.29.5 o-xylene 39.9 3.7 p-xylene 35.4 3.3 C9 aromatics total 506.4 47.1Trimethylbenzene 503.8 46.8 Methylethylbenzene 2.5 0.2 Propylbenzene 0.00.0 C10+ aromatics 83.1 7.7

Dealkylation effluent 110 was introduced to splitter unit 20 whichseparated dealkylation effluent 110 into its component parts. Light gasstream 122 was introduced to gas separator 40 to produce light gasproduct 140 and produced hydrogen 145. Produced hydrogen 145 was splitto produce hydrogen slipstream 245 and hydrogen stream 135. Thecomposition and flow rates are shown in Table 13.

TABLE 13 Composition of streams Composition, kg/hr Stream Stream StreamStream Stream Component 122 140 145 135 245 Mass Flow 388.0 216.0 172.0113.6 58.4 Hydrogen 172.0 0.0 172.0 113.6 58.4 Light gases 216.0 216.00.0 0.0 0.0 Benzene 0.0 0.0 0.0 0.0 0.0 Toluene 0.0 0.0 0.0 0.0 0.0Ethylbenzene 0.0 0.0 0.0 0.0 0.0 Mixed xylenes 0.0 0.0 0.0 0.0 0.0m-xylene — — — — — o-xylene — — — — — p-xylene — — — — — C9 aromaticstotal 0.0 0.0 0.0 0.0 0.0 Trimethylbenzene — — — — — Methylethylbenzene— — — — — Propylbenzene — — — — — C10+ aromatics 0.0 0.0 0.0 0.0 0.0

Benzene stream 126, toluene stream 124, and C9 aromatics stream 128 wereintroduced to transalkylation reactor 30 with no surplus toluene.Hydrogen stream 135 was introduced to transalkylation reactor 30.Transalkylation reactor 30 was at a temperature of 400 deg C. and apressure of 30 bar (3000 kPa). The whsv was 4.2 h⁻¹. The ratio ofhydrogen gas (H₂) to hydrocarbons is 4:1 (mol/mol). The catalyst was a1-dimensional zeolite-based transalkylation catalyst. Thetransalkylation catalyst was not the same as the dealkylation catalyst.The composition of various streams are shown in Table 14.

TABLE 14 Composition of Streams Composition, kg/hr (wt % calculated withno hydrogen gas) Component Stream 120 Stream 124 Stream 126 Stream 128Stream 132 Stream 130 Mass Flow 781.1 452.5 49.7 1026.2 83.1 1642.0Hydrogen  0.0  0.0  0.0   0.0  0.0  109.0 Light hydrocarbons  0.0  0.0 0.0   0.0  0.0  109.4 (7.1) Benzene  0.0  0.0 49.7 (100)   0.0  0.0 23.0 (1.5) Toluene  0.0 452.5 (100)  0.0   0.0  0.0  277.6 (18.1)Ethylbenzene  25.4 (3.3)  0.0  0.0   0.0  0.0  25.0 (1.6) Mixed xylenes755.7 (96.7)  0.0  0.0   0.0  0.0  578.2 (37.7) m-xylene 435.1 (55.7) —— — —  332.9 (21.7) o-xylene 169.9 (21.8) — — — —  130.0 (8.5) p-xylene150.7 (19.3) — — — —  115.3 (7.5) C9 aromatics total  0.0  0.0  0.01026.2 (100.0)  0.0  519.8 (33.9) Trimethylbenzene — — — 1021.7 (99.6) — 517.8 (33.8) Methylethylbenzene — — —   4.5 (0.4) —   2.0 (0.1)Propylbenzene — — —   0.0 —   0.0 C10+ aromatics  0.0  0.0  0.0  70.883.1 (100)   0.0 (0)

The production of mixed xylenes in Example 5 was 755.7 kg/hr. Theconversion of trimethylbenzene in transalkylation reactor 30 was 51 wt%. The overall conversion of trimethylbenzene from heavy reformate feed100 to mixed xylene stream 120 is 100 wt %. In other words, alltrimethylbenzene in heavy reformate feed 100 is converted to xylenes inmixed xylene stream 120.

Comparing the production of mixed xylenes in Example 4 and Example 5shows the increased yield due to the addition of surplus toluene totransalkylation reactor 30.

Example 6

Example 6 was a simulation of the process to produce mixed xylenes withreference to FIG. 8. Heavy reformate feed 100, having the composition inTable 15, was introduced to dealkylation reactor 10 along with hydrogenfeed 105. The flow rate of hydrogen feed 105 was 138.6 kg/hr with 66.5kg/hr hydrogen gas and 72.0 kg/hr light hydrocarbons.

TABLE 15 Composition of heavy reformate feed 100 Component Composition,kg/hr Composition, wt % Mass Flow 1000.0 100 Hydrogen 0 0.0 Light gases0 0.0 Benzene 0 0.0 Toluene 0 0.0 Ethylbenzene 0.5 0.0 Mixed xylenes51.8 5.2 m-xylene 31.8 3.2 o-xylene 10.0 1.0 p-xylene 10.0 1.0 C9aromatics total 801.6 80.2 Trimethylbenzene 565.5 56.5Methylethylbenzene 210.9 21.1 Propylbenzene 25.2 2.5 C10+ aromatics146.2 14.6

Dealkylation reactor 10 was at a temperature of 400 deg C. and apressure of 30 bar (3000 kPa). The whsv was 4.2 hr⁻¹. The ratio ofhydrogen gas (H₂) to hydrocarbons was 4:1 (mol/mol). The catalyst was a3-dimensional zeolite-based dealkylation catalyst. The composition ofdealkylation effluent 110 is shown in Table 16.

TABLE 16 Composition of dealkylation effluent 110 Composition, wt %calculated without Component Composition, kg/hr hydrogen gas Mass Flow1138.6 — Hydrogen 63.0 — Light gases 106.5 9.9 Benzene 26.8 2.5 Toluene174.9 16.3 Ethylbenzene 0.4 0.0 Mixed xylenes 177.5 16.5 m-xylene 102.29.5 o-xylene 39.9 3.7 p-xylene 35.4 3.3 C9 aromatics total 506.4 47.1Trimethylbenzene 503.8 46.8 Methylethylbenzene 2.5 0.2 Propylbenzene 0.00.0 C10+ aromatics 83.1 7.7

Dealkylation effluent 110 was introduced to splitter unit 20 whichseparated dealkylation effluent 110 into its component parts. Light gasstream 122 was introduced to gas separator 40 to produce light gasproduct 140 and produced hydrogen 145. Produced hydrogen 145 was splitto produce hydrogen slipstream 245 and hydrogen stream 135. Thecomposition and flow rates are shown in Table 17.

TABLE 17 Composition of streams Composition, kg/hr Stream Stream StreamStream Stream Component 122 140 145 135 245 Mass Flow 361.7 207.7 154.094.3 59.7 Hydrogen 154.0 0.0 154.0 94.3 59.7 Light gases 207.7 207.7 0.00.0 0.0 Benzene 0.0 0.0 0.0 0.0 0.0 Toluene 0.0 0.0 0.0 0.0 0.0Ethylbenzene 0.0 0.0 0.0 0.0 0.0 Mixed xylenes 0.0 0.0 0.0 0.0 0.0m-xylene — — — — — o-xylene — — — — — p-xylene — — — — — C9 aromaticstotal 0.0 0.0 0.0 0.0 0.0 Trimethylbenzene — — — — — Methylethylbenzene— — — — — Propylbenzene — — — — — C10+ aromatics 0.0 0.0 0.0 0.0 0.0

Benzene stream 126 and toluene stream 124 were introduced totransalkylation reactor 30 with no surplus toluene. Hydrogen stream 135was introduced to transalkylation reactor 30. C9 aromatics slip stream228 was separated from C9 aromatics stream 128 with the remaining flowof C9 aromatics stream 128 introduced to transalkylation reactor 30. C9aromatics slip stream 228 was adjusted to maintain a methyl to aromaticring ratio of 2 in transalkylation reactor 30 in the absence of an addedaromatic stream. Transalkylation reactor 30 was at a temperature of 400deg C. and a pressure of 30 bar (3000 kPa). The whsv was 4.2 h⁻¹. Theratio of hydrogen gas (H₂) to hydrocarbons is 4:1 (mol/mol). Thecatalyst was a 1-dimensional zeolite-based transalkylation catalyst. Thetransalkylation catalyst was not the same as the dealkylation catalyst.The composition of various streams are shown in Table 18.

TABLE 18 Composition of Streams Composition, kg/hr (wt % calculated withno hydrogen gas) Component Stream 120 Stream 124 Stream 126 Stream 128Stream 228 Stream 132 Stream 130 Mass Flow 672.9 444.0 53.6 859.7 115.283.1 1336.3 Hydrogen  0.0  0.0  0.0  0.0  0.0  0.0  91.0 Lighthydrocarbons  0.0  0.0  0.0  0.0  0.0  0.0  101.2 (8.1) Benzene  0.0 0.0 53.6 (100)  0.0  0.0  0.0  26.8 (2.2) Toluene  0.0 444.0 (100)  0.0 0.0  0.0  0.0  269.1 (21.6) Ethylbenzene  22.6 (3.4)  0.0  0.0  0.0 0.0  0.0  22.2 (1.8) Mixed xylenes 650.3 (96.6)  0.0  0.0  0.0  0.0 0.0  472.8 (38.0) m-xylene 374.4 (55.6) — — — — —  272.2 (21.9)o-xylene 146.2 (21.7) — — — — —  106.3 (8.5) p-xylene 129.7 (19.3) — — —— —  94.3 (7.6) C9 aromatics total  0.0  0.0  0.0 859.7 (100.0) 115.2(100.0)  0.0  353.3 (28.4) Trimethylbenzene — — — 855.6 (99.5) 114.7(99.6) —  351.8 (28.2) Methylethylbenzene — — —  4.1 (0.5)  0.5 (0.4) —  1.6 (0.1) Propylbenzene — — —  0.0  0.0 —   0.0 C10+ aromatics  0.0 0.0  0.0  70.8  0.0 83.1 (100)   0.0 (0)

The production of mixed xylenes in Example 6 was 650.3 kg/hr. Theoverall conversion of trimethylbenzene is 80 wt %.

Comparing the production rate of mixed xylenes in Example 5 and Example6 shows that introducing the entire flow rate of the C9 aromatics streaminto the transalkylation reactor increases production of mixed xylenes.

Example 7

Example 7 was a comparative example in the absence of a splitter unitbetween the dealkylation reactor and transalkylation reactor withreference to FIG. 9. Heavy reformate feed 100, having the composition inTable 19, was introduced to dealkylation reactor 10 along with hydrogenfeed 105. The flow rate of hydrogen feed 105 was 138.6 kg/hr with 66.5kg/hr hydrogen gas and 72.0 kg/hr light hydrocarbons.

TABLE 19 Composition of heavy reformate feed 100 Component Composition,kg/hr Composition, wt % Mass Flow 1000.0 100 Hydrogen 0 0.0 Light gases0 0.0 Benzene 0 0.0 Toluene 0 0.0 Ethylbenzene 0.5 0.0 Mixed xylenes51.8 5.2 m-xylene 31.8 3.2 o-xylene 10.0 1.0 p-xylene 10.0 1.0 C9aromatics total 801.6 80.2 Trimethylbenzene 565.5 56.5Methylethylbenzene 210.9 21.1 Propylbenzene 25.2 2.5 C10+ aromatics146.2 14.6

Dealkylation reactor 10 was at a temperature of 400 deg C. and apressure of 30 bar (3000 kPa). The whsv was 4.2 hr⁻¹. The ratio ofhydrogen gas (H₂) to hydrocarbons was 4:1 (mol/mol). The catalyst was a3-dimensional zeolite-based dealkylation catalyst. The composition ofdealkylation effluent 110 is shown in Table 20.

TABLE 20 Composition of dealkylation effluent 110 Composition, wt %calculated without Component Composition, kg/hr hydrogen gas Mass Flow1138.6 — Hydrogen 63.0 — Light gases 106.5 9.9 Benzene 26.8 2.5 Toluene174.9 16.3 Ethylbenzene 0.4 0.0 Mixed xylenes 177.5 16.5 m-xylene 102.29.5 o-xylene 39.9 3.7 p-xylene 35.4 3.3 C9 aromatics total 506.4 47.1Trimethylbenzene 503.8 46.8 Methylethylbenzene 2.5 0.2 Propylbenzene 0.00.0 C10+ aromatics 83.1 7.7

Dealkylation effluent 110 was introduced to transalkylation reactor 30.Transalkylation reactor 30 was at a temperature of 400 deg C. and apressure of 30 bar (3000 kPa). The whsv was 4.2 h⁻¹. The ratio ofhydrogen gas (H₂) to hydrocarbons is 4:1 (mol/mol). The catalyst was a1-dimensional zeolite-based transalkylation catalyst. Thetransalkylation catalyst was not the same as the dealkylation catalyst.Transalkylation product 930 was introduced to splitter unit 20 whichseparated transalkylation product 930 into its component parts: mixedxylenes fraction 920, light gases fraction 922, toluene fraction 924,benzene fraction 926, C9 aromatics fraction 928, and C10+ aromaticsfraction 932. The composition of various streams are shown in Table 21.

TABLE 21 Composition of Streams Composition, kg/hr (wt % calculatedwithout hydrogen gas) Component Stream 930 Stream 920 Stream 922 Stream924 Stream 926 Stream 928 Stream 932 Mass Flow 1138.6 425.9 155.5 308.142.1 161.3 45.7 Hydrogen  60.8  0.0  60.8  0.0  0.0  0.0  0.0 Lighthydrocarbons  94.7 (8.8)  0.0  94.7 (100)  0.0  0.0  0.0  0.0 Benzene 42.1 (3.9)  0.0  0.0  0.0 42.1 (100)  0.0  0.0 Toluene  308.1 (28.6) 0.0  0.0 308.1 (100)  0.0  0.0  0.0 Ethylbenzene  20.1 (1.9)  20.1(4.7)  0.0  0.0  0.0  0.0  0.0 Mixed xylenes  405.8 (37.6) 405.8 (95.3) 0.0  0.0  0.0  0.0  0.0 m-xylene  233.6 (21.7) 233.6 (54.9) — — — — —o-xylene  91.2 (8.5)  91.2 (21.4) — — — — — p-xylene  80.9 (7.5)  80.9(19.0) — — — — — C9 aromatics total  161.3 (15.0)  0.0  0.0  0.0  0.0161.3 (100.0)  0.0 Trimethylbenzene  160.2 (14.9) — — — — 160.2 (99.3) —Methylethylbenzene   1.1 (0.1) — — — —  1.1 (0.7) — Propylbenzene   0.0— — — —  0.0 — C10+ aromatics  45.7 (4.2)  0.0  0.0  0.0  0.0  0.0 45.7(100)

The production of mixed xylenes was 405.8 kg/hr. The overall conversionof trimethylbenzene is 72 wt %.

Comparing the production rate of mixed xylenes in Example 4 and Example7 shows that the addition of a splitter unit and the associated processstream configuration changes unexpectedly and advantageously increasesthe production rate of mixed xylenes by about 100%.

Example 8

Example 8 illustrates the xylene production process with energyoptimization with reference to FIG. 10. Example 8 was simulated usingAspen Plus®. The compositions and temperatures of the streams are shownin Table 22.

TABLE 22 Stream temperature and composition 100 200 105 205 210 215 110220 225 230 Temperature C. 44 115 38 88 344 400 400 130 96 42 Mass Flowkg/hr 1000 1000 137 1137 1137 1137 1137 1137 1137 1137 Hydrogen kg/hr 00 66 66 66 66 62 62 62 62 C1-C5 kg/hr 0 0 71 71 71 71 155 155 155 155Benzene kg/hr 0 0 0 0 0 0 25 25 25 25 Toluene kg/hr 0 0 0 0 0 0 169 169169 169 Ethylbenzene kg/hr 0 0 0 0 0 0 0 0 0 0 Xylenes Total kg/hr 0 0 00 0 0 116 116 116 116 m-xylene kg/hr 0 0 0 0 0 0 67 67 67 67 o-xylenekg/hr 0 0 0 0 0 0 26 26 26 26 p-xylene kg/hr 0 0 0 0 0 0 23 23 23 23 C9aromatics Total kg/hr 846 846 0 846 846 846 534 534 534 534 MEB kg/hr223 223 0 223 223 223 223 223 223 223 TMB kg/hr 597 597 0 597 597 597531 531 531 531 Propylbenzene kg/hr 27 27 0 27 27 27 0 0 0 0 C10+ kg/hr154 154 0 154 154 154 77 77 77 77 Total HC Flow kg/hr 1000 1000 71 10711071 1071 1075 1075 1075 1075 240 247 140 126 120 128 132 124 135 250Temperature C. 42 115 115 115 150 150 115 150 38 137 Mass Flow kg/hr 949949 72 37 765 1131 65 586 20 1737 Hydrogen kg/hr 0 0 0 0 0 0 0 0 20 20C1-C5 kg/hr 35 35 72 0 0 0 0 0 0 0 Benzene kg/hr 24 24 0 37 0 0 0 37 037 Toluene kg/hr 166 166 0 0 0 0 0 549 0 549 Ethylbenzene kg/hr 0 0 0 030 0 0 0 0 0 Xylenes Total kg/hr 115 115 0 0 735 0 0 0 0 0 m-xylenekg/hr 66 66 0 0 423 0 0 0 0 0 o-xylene kg/hr 26 26 0 0 165 0 0 0 0 0p-xylene kg/hr 23 23 0 0 146 0 0 0 0 0 C9 aromatics Total kg/hr 533 5330 0 0 1065 0 0 0 1065 MEB kg/hr 3 3 0 0 0 5 0 0 0 5 TMB kg/hr 530 530 00 0 1060 0 0 0 1060 Propylbenzene kg/hr 0 0 0 0 0 0 0 0 0 0 C10+ kg/hr77 77 0 0 0 65 65 0 0 65 Total HC Flow kg/hr 949 949 72 37 765 1131 65586 0 1717 255 260 130 265 270 275 280 285 290 295 Temperature C. 380400 400 151 93 40 40 115 60 40 Mass Flow kg/hr 1737 1737 1737 1737 17371737 1707 1707 765 765 Hydrogen kg/hr 20 20 16 16 16 16 0 0 0 0 C1-C5kg/hr 0 0 50 50 50 50 37 37 0 0 Benzene kg/hr 37 37 52 52 52 52 51 51 00 Toluene kg/hr 549 549 384 384 384 384 383 383 0 0 Ethylbenzene kg/hr 00 30 30 30 30 30 30 30 30 Xylenes Total kg/hr 0 0 620 620 620 620 619619 735 735 m-xylene kg/hr 0 0 357 357 357 357 357 357 423 423 o-xylenekg/hr 0 0 139 139 139 139 139 139 165 165 p-xylene kg/hr 0 0 124 124 124124 123 123 146 146 C9 aromatics Total kg/hr 1065 1065 533 533 533 533533 533 0 0 MEB kg/hr 5 5 3 3 3 3 3 3 0 0 TMB kg/hr 1060 1060 530 530530 530 530 530 0 0 Propylbenzene kg/hr 0 0 0 0 0 0 0 0 0 0 C10+ kg/hr65 65 53 53 53 53 53 53 0 0 Total HC Flow kg/hr 1717 1717 1721 1721 17211721 1707 1707 765 765

Example 9

Example 9 illustrates the xylene production process with energyoptimization with reference to FIG. 11 and FIG. 10. Example 9 wassimulated using Aspen Plus®. The compositions and temperatures of thestreams are shown in Table 23.

TABLE 23 Stream temperature and compositions. 100 200 105 205 207 209210 215 110 220 225 Temperature C. 44 78 38 64 80 108 369 400 400 125 90Mass Flow kg/hr 1000 1000 137 1137 1137 1137 1137 1137 1137 1137 1137Hydrogen kg/hr 0 0 66 66 66 66 66 66 62 62 62 C1-C5 kg/hr 0 0 71 71 7171 71 71 155 155 155 Benzene kg/hr 0 0 0 0 0 0 0 0 25 25 25 Toluenekg/hr 0 0 0 0 0 0 0 0 169 169 169 Ethylbenzene kg/hr 0 0 0 0 0 0 0 0 0 00 Xylenes Total kg/hr 0 0 0 0 0 0 0 0 116 116 116 m-xylene kg/hr 0 0 0 00 0 0 0 67 67 67 o-xylene kg/hr 0 0 0 0 0 0 0 0 26 26 26 p-xylene kg/hr0 0 0 0 0 0 0 0 23 23 23 C9 aromatics Total kg/hr 846 846 0 846 846 846846 846 534 534 534 MEB kg/hr 223 223 0 223 223 223 223 223 3 3 3 TMBkg/hr 597 597 0 597 597 597 597 597 531 531 531 Propylbenzene kg/hr 2727 0 27 27 27 27 27 0 0 0 C10+ kg/hr 154 154 0 154 154 154 154 154 77 7777 Total HC Flow kg/hr 1000 1000 71 1071 1071 1071 1071 1071 1075 10751075 227 230 240 247 140 126 120 128 132 124 135 250 255 Temperature C.76 42 42 115 115 115 150 150 115 150 38 137 383 Mass Flow kg/hr 11371137 949 949 72 37 765 1131 65 586 20 1737 1737 Hydrogen kg/hr 62 62 0 00 0 0 0 0 0 20 20 20 C1-C5 kg/hr 155 155 35 35 72 0 0 0 0 0 0 0 0Benzene kg/hr 25 25 24 24 0 37 0 0 0 37 0 37 37 Toluene kg/hr 169 169166 166 0 0 0 0 0 549 0 549 549 Ethylbenzene kg/hr 0 0 0 0 0 0 30 0 0 00 0 0 Xylenes Total kg/hr 116 116 115 115 0 0 735 0 0 0 0 0 0 m-xylenekg/hr 67 67 66 66 0 0 423 0 0 0 0 0 0 o-xylene kg/hr 26 26 26 26 0 0 1650 0 0 0 0 0 p-xylene kg/hr 23 23 23 23 0 0 146 0 0 0 0 0 0 C9 aromaticskg/hr 534 534 533 533 0 0 0 1065 0 0 0 1065 1065 Total MEB kg/hr 3 3 3 30 0 0 5 0 0 0 5 5 TMB kg/hr 531 531 530 530 0 0 0 1060 0 0 0 1060 1060Propylbenzene kg/hr 0 0 0 0 0 0 0 0 0 0 0 0 0 C10+ kg/hr 77 77 77 77 0 00 65 65 0 0 65 65 Total HC Flow kg/hr 1075 1075 949 949 72 37 765 113165 586 0 1717 1717 260 130 265 270 272 275 280 285 292 295 TemperatureC. 400 400 148 89 72 40 40 115 90 40 Mass Flow kg/hr 1737 1737 1737 17371737 1737 1707 1707 765 765 Hydrogen kg/hr 20 16 16 16 16 16 0 0 0 0C1-C5 kg/hr 0 50 50 50 50 50 37 37 0 0 Benzene kg/hr 37 52 52 52 52 5251 51 0 0 Toluene kg/hr 549 384 384 384 384 384 383 383 0 0 Ethylbenzenekg/hr 0 30 30 30 30 30 30 30 30 30 Xylenes Total kg/hr 0 620 620 620 620620 619 619 735 735 m-xylene kg/hr 0 357 357 357 357 357 357 357 423 423o-xylene kg/hr 0 139 139 139 139 139 139 139 165 165 p-xylene kg/hr 0124 124 124 124 124 123 123 146 146 C9 aromatics Total kg/hr 1065 533533 533 533 533 533 533 0 0 MEB kg/hr 5 3 3 3 3 3 3 3 0 0 TMB kg/hr 1060530 530 530 530 530 530 530 0 0 Propylbenzene kg/hr 0 0 0 0 0 0 0 0 0 0C10+ kg/hr 65 53 53 53 53 53 53 53 0 0 Total HC Flow kg/hr 1717 17211721 1721 1721 1721 1707 1707 765 765

Example 10

Example 10 is a comparative example that illustrates a xylene productionprocess in the absence of energy optimization with reference to FIG. 12and FIG. 10. Example 9 was simulated using Aspen Plus®.

In a process according to FIG. 12, heavy reformate 100 is heated infirst process heater 10-7 to produce hot feed stream 200. Hot feedstream 200 and hydrogen feed 105 are mixed to produce mixed feed 205.Mixed feed 205 is heated in second process heater 10-8 to produce hotmixed feed 210. Hot mixed feed 210 is heated in feed fired heater 10-3to produce hot reactor feed 215. Hot reactor feed 215 is reacted indealkylation reactor 10 to produce dealkylation effluent 110.Dealkylation effluent 110 is cooled in effluent cooler 20-1 to producedmixed effluent stream 230. Hydrogen in mixed effluent stream 230 isseparated in effluent separator 20-2 to produce produced hydrogen 145and separated effluent 240. Separated effluent 240 is heated in thirdprocess heater 20-7 to produce dealkylation splitter feed 247.Dealkylation splitter feed 247 is separated in splitter unit 20 toproduce light gas product 140, toluene stream 124, benzene stream 126,C9 aromatics stream 128, C10+ aromatics stream 132, and mixed xylenestream 120. Toluene stream 124, C9 aromatics stream 128, and hydrogenstream 135 are mixed in mixer 30-1 to produce mixed transalkylation feed250. Mixed transalkylation feed 250 is heated in fourth process heater30-4 to produce hot transalkylation feed 255. Hot transalkylation feed255 is heated in transalkylation fired heater 30-3 to producetransalkylation feed 260. Transalkylation feed 260 is reacted intransalkylation reactor 30 to produce transalkylation effluent 130.Transalkylation effluent 130 is cooled in transalkylation cooler 20-4 toproduce cooled mixed effluent 275. Light gases stream 235 are separatedin transalkylation separator 20-5 to produce separated transalkylationeffluent 280. Separated transalkylation effluent 280 is heated in fifthprocess heater 20-8 to produce transalkylation splitter feed 285. Mixedxylene stream 120 is cooled in xylene cooler 10-4 to produce mixedxylene product 295. The stream temperature and compositions are in Table24.

TABLE 24 Stream temperature and compositions. 100 200 105 205 210 215110 230 Temperature C. 44 115 38 87 200 400 400 42 Mass Flow kg/hr 10001000 137 1137 1137 1137 1137 1137 Hydrogen kg/hr 0 0 66 66 66 66 62 62C1-C5 kg/hr 0 0 71 71 71 71 155 155 Benzene kg/hr 0 0 0 0 0 0 25 25Toluene kg/hr 0 0 0 0 0 0 169 169 Ethylbenzene kg/hr 0 0 0 0 0 0 0 0Xylenes Total kg/hr 0 0 0 0 0 0 116 116 m-xylene kg/hr 0 0 0 0 0 0 67 67o-xylene kg/hr 0 0 0 0 0 0 26 26 p-xylene kg/hr 0 0 0 0 0 0 23 23 C9aromatics kg/hr 846 846 0 846 846 846 534 534 Total MEB kg/hr 223 223 0223 223 223 3 3 TMB kg/hr 597 597 0 597 597 597 531 531 Propyl- kg/hr 2727 0 27 27 27 0 0 benzene C10+ kg/hr 154 154 0 154 154 154 77 77 TotalHC kg/hr 1000 1000 71 1071 1071 1071 1075 1075 Flow 240 247 140 126 120128 132 124 135 Temperature C. 42 115 115 115 150 150 115 150 38 MassFlow kg/hr 949 949 72 37 765 1131 65 586 20 Hydrogen kg/hr 0 0 0 0 0 0 00 20 C1-C5 kg/hr 35 35 72 0 0 0 0 0 0 Benzene kg/hr 24 24 0 37 0 0 0 370 Toluene kg/hr 166 166 0 0 0 0 0 549 0 Ethylbenzene kg/hr 0 0 0 0 30 00 0 0 Xylenes Total kg/hr 115 115 0 0 735 0 0 0 0 m-xylene kg/hr 66 66 00 423 0 0 0 0 o-xylene kg/hr 26 26 0 0 165 0 0 0 0 p-xylene kg/hr 23 230 0 146 0 0 0 0 C9 aromatics kg/hr 533 533 0 0 0 1065 0 0 0 Total MEBkg/hr 3 3 0 0 0 5 0 0 0 TMB kg/hr 530 530 0 0 0 1060 0 0 0 Propylbenzenekg/hr 0 0 0 0 0 0 0 0 0 C10+ kg/hr 77 77 0 0 0 65 65 0 0 Total HC Flowkg/hr 949 949 72 37 765 1131 65 586 0 250 255 260 130 275 280 285 295Temperature C. 137 200 400 400 40 40 115 40 Mass Flow kg/hr 1737 17371737 1737 1737 1707 1707 765 Hydrogen kg/hr 20 20 20 16 16 0 0 0 C1-C5kg/hr 0 0 0 50 50 37 37 0 Benzene kg/hr 37 37 37 52 52 51 51 0 Toluenekg/hr 549 549 549 384 384 383 383 0 Ethylbenzene kg/hr 0 0 0 30 30 30 3030 Xylenes kg/hr 0 0 0 620 620 619 619 735 Total m-xylene kg/hr 0 0 0357 357 357 357 423 o-xylene kg/hr 0 0 0 139 139 139 139 165 p-xylenekg/hr 0 0 0 124 124 123 123 146 C9 aromatics kg/hr 1065 1065 1065 533533 533 533 0 Total MEB kg/hr 5 5 5 3 3 3 3 0 TMB kg/hr 1060 1060 1060530 530 530 530 0 Propylben- kg/hr 0 0 0 0 0 0 0 0 zene C10+ kg/hr 65 6565 53 53 53 53 0 Total HC kg/hr 1717 1717 1717 1721 1721 1707 1707 765Flow

Aspen Energy Analyzer was used to determine values for the heatexchanger network design in each of Examples 8, 9, and 10. The valuesare shown in Table 25.

TABLE 25 Heat exchanger values Example FIG. Area (m²) Shells Heating(kJ/h) Cooling (kJ/h) 8 10 216 35   291,113   397,858 9 11 369 47  185,694    292428 10 12 37 18 3,432,166 3,538,909

As can be seen in Table 25, the process according to Example 10 requires91.5% more heat input than the process of Example 8 and 94.5% more heatinput than the process of Example 9. The process according to Example 10requires 88.7% more cooling input than the process of Example 8 and91.7% more cooling input.

Although the embodiments have been described in detail, it should beunderstood that various changes, substitutions, and alterations can bemade without departing from the principle and scope. Accordingly, thescope of the present embodiments should be determined by the followingclaims and their appropriate legal equivalents.

There various elements described can be used in combination with allother elements described here unless otherwise indicated.

The singular forms “a”, “an” and “the” include plural referents, unlessthe context clearly dictates otherwise.

Optional or optionally means that the subsequently described event orcircumstances may or may not occur. The description includes instanceswhere the event or circumstance occurs and instances where it does notoccur.

Ranges may be expressed here as from about one particular value to aboutanother particular value and are inclusive unless otherwise indicated.When such a range is expressed, it is to be understood that anotherembodiment is from the one particular value to the other particularvalue, along with all combinations within said range.

Throughout this application, where patents or publications arereferenced, the disclosures of these references in their entireties areintended to be incorporated by reference into this application, in orderto more fully describe the state of the art to which the inventionpertains, except when these references contradict the statements madehere.

As used here and in the appended claims, the words “comprise,” “has,”and “include” and all grammatical variations thereof are each intendedto have an open, non-limiting meaning that does not exclude additionalelements or steps.

That which is claimed is:
 1. A system for producing mixed xylenes from aheavy reformate feed, the system comprising: a feed exchanger, the feedexchanger configured to transfer heat from a mixed xylene stream to theheavy reformate feed to increase a temperature of the heavy reformatefeed to produce a hot feed stream, wherein the feed exchanger is a crossprocess exchanger, wherein the heavy reformate comprises aromatichydrocarbons with nine or more carbon atoms (C9+ aromatics), wherein thehydrogen feed comprises hydrogen gas, wherein a temperature of the mixedxylene stream is reduced to produce a cooled mixed stream; a mixingpoint fluidly connected to the feed exchanger, the mixing pointconfigured to mix the hot feed stream and a hydrogen feed to produce amixed feed; a feed-effluent exchanger fluidly connected to the mixingpoint, the feed-effluent exchanger configured to transfer heat from adealkylation effluent to the mixed feed to increase a temperature of themixed feed to produce a hot mixed feed, wherein the feed-effluentexchanger is a cross process exchanger, wherein a temperature of thedealkylation effluent is reduced to produce a cooled effluent stream; afeed fired heater fluidly connected to the feed-effluent exchanger, thefeed fired heater configured to increase a temperature of the hot mixedfeed to produce a hot reactor feed; a dealkylation reactor fluidlyconnected to the feed fired heater, the dealkylation reactor configuredto react the heavy reformate feed with the hydrogen gas in the presenceof a dealkylation catalyst in the dealkylation reactor to produce thedealkylation effluent, wherein the dealkylation reactor is at adealkylation temperature, wherein the dealkylation reactor is at adealkylation pressure, wherein the dealkylation reactor has a liquidhourly space velocity; an effluent-separator exchanger fluidly connectedto the feed-effluent exchanger, the effluent-separator exchangerconfigured to transfer heat from the cooled effluent stream to aseparated effluent to reduce the temperature of the cooled effluentstream to produce an effluent stream, wherein the effluent-separatorexchanger is a cross process exchanger, wherein a temperature of theseparated effluent is increased in the effluent-separator exchanger toproduce a dealkylation splitter feed; transalkylation effluent toproduce a cooled effluent, wherein a temperature of the separatedtransalkylation effluent is increased in the effluent transalkylationexchanger to produce a transalkylation splitter feed, wherein theeffluent-transalkylation exchanger is a cross process exchanger, whereinthe effluent-transalkylation reactor is fluidly connected to thesplitter unit; a transalkylation cooler fluidly connected to theeffluent-transalkylation heater, the transalkylation cooler configuredto reduce a temperature of the cooled effluent to produce a cooled mixedeffluent; a transalkylation separator fluidly connected to thetransalkylation cooler, the transalkylation separator configured toseparate the cooled mixed effluent to produce a separatedtransalkylation effluent and a light gases stream; and a xylene coolerfluidly connected to the feed exchanger, the xylene cooler configured toreduce the temperature of the cooled mixed stream to produce a mixedxylene product.
 2. The system of claim 1, wherein a temperature of thehot mixed feed is between 324 deg C. and 344 deg C., and further whereina temperature of the hot reactor feed is between 380 deg C. and 400 degC.
 3. The system of claim 1, wherein a temperature of the cooledeffluent stream is between 115 deg C. and 145 deg C., wherein atemperature of the effluent stream is between 80 deg C. and 110 deg C.,and further wherein a temperature of the mixed effluent stream isbetween 38 deg C. and 47 deg C.
 4. The system of claim 1, wherein atemperature of the hot transalkylation feed is between 330 deg C. and390 deg C., and further wherein a temperature of the transalkylationfeed is between 380 deg C. and 400 deg C.
 5. The system of claim 1,wherein a temperature of the cooled transalkylation effluent between 136deg C. and 166 deg C., wherein a temperature of the cooled effluent isbetween 83 deg C. and 103 deg C., wherein a temperature of the cooledmixed effluent is between 35 deg C. and 45 deg C., and further wherein atemperature of the transalkylation splitter feed is between 105 deg C.and 125 deg C.
 6. The system of claim 1, wherein a temperature of thecooled mixed stream is between 55 deg C. and 65 deg C., and furtherwherein a temperature of the mixed xylene product is between 30 deg C.and 50 deg C.
 7. The system of claim 1, wherein the dealkylationtemperature is between 200 deg C. and 500 deg C., wherein thedealkylation pressure is between 5 bar and 40 bar, and wherein theliquid hourly space velocity in the dealkylation reactor is between 1hr−1 and 10 hr−1.
 8. The system of claim 1, wherein the transalkylationtemperature is between 300 deg C. and 500 deg C., wherein thetransalkylation pressure is between 10 bar and 40 bar, wherein theliquid hourly space velocity in the transalkylation reactor is between0.5 hr−1 and 6 hr−1.
 9. A system for producing mixed xylenes from aheavy reformate feed, the system comprising: a feed exchanger, the feedexchanger configured to transfer heat from a cooled effluent to theheavy reformate feed to increase a temperature of the heavy reformatefeed to produce a hot feed stream, wherein the feed exchanger is a crossprocess exchanger, wherein the heavy reformate comprises aromatichydrocarbons with nine or more carbon atoms (C9+ aromatics), wherein thehydrogen feed comprises hydrogen gas, wherein a temperature of thecooled effluent is reduced to produce a mixed effluent stream; a mixingpoint fluidly connected to the feed exchanger, the mixing pointconfigured to mix the hot feed stream and a hydrogen feed to produce amixed feed; a feed cross exchanger fluidly connected to the mixingpoint, the feed cross exchanger configured to transfer heat from aneffluent stream to the mixed feed to increase a temperature of the mixedfeed to produce a heated mixed feed, wherein the feed cross exchanger isa cross process exchanger, wherein a temperature of the effluent streamis reduced in the feed cross exchanger to produce a warm effluent; afeed-xylene exchanger fluidly connected to the feed cross exchanger, thefeed-xylene exchanger configured to transfer heat from a mixed xylenesto the heated mixed feed to increase a temperature of the heated mixedfeed to produce a warm mixed feed, wherein the feed-xylene exchanger isa cross process exchanger, wherein a temperature of the mixed xylenes isreduced in the feed-xylene exchanger to produce a cooled xylene stream;a feed-effluent exchanger fluidly connected to the feed-xyleneexchanger, the feed-effluent exchanger configured to transfer heat froma dealkylation effluent to the warm mixed feed to increase a temperatureof the warm mixed feed to produce a hot mixed feed, wherein thefeed-effluent exchanger is a cross process exchanger, wherein atemperature of the dealkylation effluent is reduced to produce a cooledeffluent stream; a feed fired heater fluidly connected to thefeed-effluent exchanger, the feed fired heater configured to increase atemperature of the hot mixed feed to produce a hot reactor feed; adealkylation reactor fluidly connected to the feed fired heater, thedealkylation reactor configured to react the heavy reformate feed withthe hydrogen gas in the presence of a dealkylation catalyst in thedealkylation reactor to produce the dealkylation effluent, wherein thedealkylation reactor is at a dealkylation temperature, wherein thedealkylation reactor is at a dealkylation pressure, wherein thedealkylation reactor has a liquid hourly space velocity; aneffluent-separator exchanger fluidly connected to the feed-effluentexchanger, the effluent-separator exchanger configured to transfer heatfrom the cooled effluent stream to a separated effluent to reduce thetemperature of the cooled effluent stream to produce an effluent stream,wherein the effluent-separator exchanger is a cross process exchanger,wherein a temperature of the separated effluent is increased in theeffluent-separator exchanger to produce a dealkylation splitter feed; aneffluent cooler fluidly connected to the feed cross exchanger, theeffluent cooler configured to reduce a temperature of the warm effluentstream to produce a mixed effluent stream; an effluent separator fluidlyconnected to the effluent cooler, the effluent separator configured toseparate the mixed effluent stream to produce a produced hydrogen and aseparated effluent, wherein the produced hydrogen comprises hydrogen; asplitter unit fluidly connected to the effluent-separator exchanger, thesplitter unit configured to separate the dealkylation splitter feed intoa light gas product, a toluene stream, a benzene stream, a C9 aromaticsstream, a C10+ aromatics stream, and a mixed xylene stream in thesplitter unit, wherein the light gas product comprises lighthydrocarbons and hydrogen, wherein the toluene stream comprises toluene,wherein the benzene stream comprises benzene, wherein the mixed xylenestream comprises mixed xylenes, wherein the C9 stream comprises C9aromatics, wherein the C10+ aromatics stream comprises C10+ aromatics; amixer fluidly connected to the splitter unit, the mixer configured tomix the toluene stream, the C9 aromatics stream, and a hydrogen streamto produce a mixed transalkylation feed, wherein the hydrogen streamcomprises hydrogen gas; a C9-effluent heater fluidly connected to themixer, the C9-effluent heater configured to transfer heat from atransalkylation effluent to the mixed transalkylation feed to increase atemperature of the mixed transalkylation feed to produce a hottransalkylation feed, wherein the C9-effluent heater is a cross processexchanger, wherein a temperature of the transalkylation effluent isreduced in the C9-effluent heater to produce a cooled transalkylationeffluent; a transalkylation fired heater fluidly connected to theC9-effluent heater, the transalkylation fired heater configured toincrease a temperature of the hot transalkylation feed to produce atransalkylation feed; a transalkylation reactor fluidly connected to thetransalkylation fired heater, the transalkylation reactor configured toreact the toluene and the C9 aromatics in the presence of atransalkylation catalyst to produce a transalkylation effluent, whereinthe transalkylation reactor is at a transalkylation temperature, whereinthe transalkylation reactor is at a transalkylation pressure, whereinthe transalkylation reactor has a liquid hourly space velocity; aneffluent-transalkylation exchanger fluidly connected to the C9-effluentheater, the effluent-transalkylation exchanger configured to transferheat from the cooled transalkylation effluent to the separatedtransalkylation effluent to reduce a temperature of the cooledtransalkylation effluent to produce a cooled effluent, wherein atemperature of the separated transalkylation effluent is increased inthe effluent transalkylation exchanger to produce a transalkylationsplitter feed, wherein the effluent-transalkylation exchanger is a crossprocess exchanger, wherein the effluent-transalkylation reactor isfluidly connected to the splitter unit; a transalkylation cooler fluidlyconnected to the feed exchanger, the transalkylation cooler configuredto reduce a temperature of the mixed effluent stream to produce a cooledmixed effluent; a transalkylation separator fluidly connected to thetransalkylation cooler, the transalkylation separator configured toseparate the cooled mixed effluent to produce a separatedtransalkylation effluent and a light gases stream; and a xylene coolerfluidly connected to the feed exchanger, the xylene cooler configured toreduce the temperature of the cooled mixed stream to produce a mixedxylene product.
 10. The system of claim 9, wherein a temperature of theheated mixed feed is between 65 deg C. and 90 deg C., wherein atemperature of warm mixed feed is between 90 deg C. and 150 deg C.,wherein a temperature of the hot mixed feed is between 324 deg C. and344 deg C., and further wherein a temperature of the hot reactor feed isbetween 380 deg C. and 400 deg C.
 11. The system of claim 9, wherein atemperature of the cooled effluent stream is between 115 deg C. and 145deg C., wherein a temperature of the effluent stream is between 80 degC. and 110 deg C., wherein a temperature of the warm effluent is between65 deg C. and 80 deg C., and further wherein a temperature of the mixedeffluent stream is between 38 deg C. and 47 deg C.
 12. The system ofclaim 9, wherein a temperature of the hot transalkylation feed isbetween 330 deg C. and 390 deg C., and further wherein a temperature ofthe transalkylation feed is between 380 deg C. and 400 deg C.
 13. Thesystem of claim 9, wherein a temperature of the cooled transalkylationeffluent between 136 deg C. and 166 deg C., wherein a temperature of thecooled effluent is between 83 deg C. and 103 deg C., wherein atemperature of the mixed effluent stream is between 45 deg C. and 78 degC., wherein a temperature of the cooled mixed effluent is between 35 degC. and 45 deg C., and further wherein a temperature of thetransalkylation splitter feed is between 105 deg C. and 125 deg C. 14.The system of claim 9, wherein a temperature of the cooled xylene streamis between 55 deg C. and 65 deg C., and further wherein a temperature ofthe mixed xylene product is between 30 deg C. and 50 deg C.
 15. Thesystem of claim 9, wherein the dealkylation temperature is between 200deg C. and 500 deg C., wherein the dealkylation pressure is between 5bar and 40 bar, and wherein the liquid hourly space velocity in thedealkylation reactor is between 1 hr−1 and 10 hr−1.
 16. The system ofclaim 9, wherein the transalkylation temperature is between 300 deg C.and 500 deg C., wherein the transalkylation pressure is between 10 barand 40 bar, wherein the liquid hourly space velocity in thetransalkylation reactor is between 0.5 hr−1 and 6 hr−1.